Downtown Winter Haven Homes

• 

  

  

  /37

  $200,000

  • 3 Beds
  • 1 Bath
  • 1,040 Sq Ft

  950 Avenue O NE, Winter Haven, FL 33881

  This classic 1956 concrete block home offers 3 bedrooms and 1 bathroom, perfectly blending vintage character with everyday convenience. Featuring a covered carport with laundry room, a fully fenced yard, and plenty of space for outdoor living, this property is ideal for first-time buyers, downsizers, or investors.Located just minutes from Polk State College, shopping, dining, and vibrant

  JoJo Cobb KELLER WILLIAMS REALTY SMART 1

  950 Avenue O NE, Winter Haven, FL 33881
• 

  

  

  /6

  $1,300 per month

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Townhouse for Rent

  645 7th St NE Unit 647, Winter Haven, FL 33881

  Beautifully updated 2 bed/1 bath duplex at 647 7th St NE, Winter Haven, FL! Features modern vinyl plank flooring, granite countertops, ceiling fans in bedrooms and living area, and convenient in-unit washer/dryer hookups. Bright and spacious with 900 sq. ft., this home is ideally located near LEGOLAND, Polk State College, Downtown Winter Haven, shopping, and dining. Perfect for comfortable,

  Pedro Cartagena 1513 REALTY LLC

  645 7th St NE Unit 647, Winter Haven, FL 33881
• 

  

  /2

  $99,000 Sold Jun 06, 2025

  • 840 Sq Ft
  • $118/SF
  • 353 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1964

  1700 6th St NW Unit C31, Winter Haven, FL 33881

  FULLY FURNISHED 55+ UPDATED 2-BEDROOM CONDO **PRICE REDUCED** Welcome to this amazing NW Winter Haven end unit condo! Updates include: new windows with new wide blinds throughout, updated vinyl flooring, an updated kitchen, new water heater and updated bathrooms. Being an end unit, the front living room has beautiful natural light and the windows on two sides provide a cross breeze. The primary

  Susan Mayrant COLDWELL BANKER REALTY

  1700 6th St NW Unit C31, Winter Haven, FL 33881
• 

  

  

  /25

  Est $268,536 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,504 Sq Ft

  618 Avenue R NE, Winter Haven, FL 33881

  618 Avenue R NE, Winter Haven, FL 33881
• 

  

  

  /6

  $140,000

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  888 23rd St NW, Winter Haven, FL 33881

  Welcome to 888 23rd St NW — a charming 1949 block home brimming with potential and ready for a full rehab. Boasting 2 bedrooms, 1 bathroom, and 768 square feet, it’s an ideal canvas for investors or DIY enthusiasts to create a stunning transformation. This 2-bedroom, 1-bathroom property offers 768 square feet of living space, featuring durable laminate and ceramic tile flooring throughout.Set

  Dee Norris NEXTHOME NORRIS & COMPANY REALTY

  888 23rd St NW, Winter Haven, FL 33881
• 

  

  /8

  $1,400 per month

  • 2 Beds
  • 1 Bath
  • 840 Sq Ft
  • Apartment for Rent

  1804 3rd Ct SE, Winter Haven, FL 33880

  Very nice apartment for rent in the center of Winter Haven, FL. Located in a very good area close to all major stores.

  Othner Stfleurose OSF REAL ESTATE SERVICE

  1804 3rd Ct SE, Winter Haven, FL 33880
• 

  /2

  $230,000 Sold Jun 05, 2025

  • 1,241 Sq Ft
  • $185/SF
  • 14 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2025

  612 Sears Ave NE, Winter Haven, FL 33881

  BACK-UP OFFERS BEING ACCEPTED! Beautiful 3BR/2BA new construction single family residence located in the heart of Winter Haven. Close proximity to I-4, Tampa, and Orlando. This home boasts spray foam insultation, 30 year architectural shingles, energy efficient Low-E windows, stainless steel appliances, quartz located in the kitchen and both bathrooms, high ceilings throughout, luxury vinyl

  Stephenie Long J&S PROPERTY REALTY GROUP LLC

  612 Sears Ave NE, Winter Haven, FL 33881
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  /66

  Est $502,160 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,340 Sq Ft

  1490 1/2 N Lake Shipp Dr, Winter Haven, FL 33880

  1490 1/2 N Lake Shipp Dr, Winter Haven, FL 33880
• 

  

  /24

  $250,000

  • 3 Beds
  • 2 Baths
  • 1,540 Sq Ft

  1865 4th St SE, Winter Haven, FL 33880

  Welcome to 1865 4th St. SE, Winter Haven, FL! Step into charm and possibility with this delightful 3-bedroom, 2-bathroom home nestled in a serene neighborhood. From the moment you enter, you'll be greeted by a spacious living room bathed in natural light—perfect for cozy evenings or lively family gatherings.The kitchen offers generous cabinet space and a welcoming eat-in area, ideal for

  Nette Nelson EXP REALTY LLC

  1865 4th St SE, Winter Haven, FL 33880
• 

  

  /16

  $1,580 per month

  • 3 Beds
  • 2 Baths
  • 1,684 Sq Ft
  • House for Rent

  924 Avenue T SE, Winter Haven, FL 33880

  Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening! Take advantage of the incredible location, nestled

  Nico Silva Vanegas MAIN STREET RENEWAL LLC

  924 Avenue T SE, Winter Haven, FL 33880
• 

  /2

  $55,000 Sold Jun 03, 2025

  • Land
  • 0.4 Acre
  • $137,500 per Acre

  • 4 Days On Market

  613 Avenue O NE, Winter Haven, FL 33881

  Build your dream home or next investment property in the heart of Winter Haven. This prime vacant residential lot at 613 Ave O NE offers an outstanding opportunity for buyers, investors, and home builders alike. Located in an established neighborhood with city water and sewer nearby, this lot is ready for your vision—whether it's a custom single-family home, a long-term rental, or a profitable

  Michael Gay KELLER WILLIAMS REALTY SMART 1

  613 Avenue O NE, Winter Haven, FL 33881
• 

  

  /6

  Est $291,296 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,368 Sq Ft

  239 Krenson Bay Loop, Winter Haven, FL 33881

  239 Krenson Bay Loop, Winter Haven, FL 33881
• 

  

  /14

  $33,500

  • 2 Beds
  • 1.5 Baths
  • 800 Sq Ft

  71 Charlote Dr, Winter Haven, FL 33880

  Welcome to your beautifully updated and renovated mobile home located in a vibrant 55+ community! This charming residence features modern upgrades throughout, ensuring a comfortable and stylish living experience. Step inside to discover an open-concept floor plan that maximizes space and natural light. The updated kitchen boasts new appliances, sleek countertops, and ample cabinetry, making

  Michael Hutcheson Coast to Coast Mobile Home Sales LLC

  71 Charlote Dr, Winter Haven, FL 33880
• 

  

  /6

  $700 per month

  • 2 Beds
  • 1 Bath
  • 740 Sq Ft
  • Apartment for Rent

  720 6th St NW Unit 3, Winter Haven, FL 33881

  Rent with confidence from a licensed Real Estate Brokerage. We have a quick and simple application process. Contact us through this website or call to set up a tour and apply today!WE PROUDLY WELCOME ALL PETS.Welcome to this cute 2-bed, 1-bath home! Our spacious layout is perfect for comfortable living. Enjoy the yard to unwind after a long day, enjoy the fresh air, and gather for

  Erich Spivey ALABAMA LLC

  720 6th St NW Unit 3, Winter Haven, FL 33881
• 

  /2

  $194,000 Sold Jun 02, 2025

  • 1,120 Sq Ft
  • $173/SF
  • 62 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1947

  2237 Avenue B NW, Winter Haven, FL 33880

  Make your appointment today to view this adorable 2 bedroom home that is filled with character and situated on a spacious corner lot close to Lake Howard. This home seamlessly blends historic charm with modern updates. As you arrive, you're greeted by a charming front porch, and a double-car carport. Home features new roof (2022). Step inside to find beautiful hardwood flooring, shiplap ceilings

  Vanessa Franz Barnes KELLER WILLIAMS REALTY AT THE LAKES

  2237 Avenue B NW, Winter Haven, FL 33880
• 

  

  /27

  Est $293,541 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  139 Krenson Bay Loop, Winter Haven, FL 33881

  139 Krenson Bay Loop, Winter Haven, FL 33881
• 

  

  /73

  $260,000

  • 2 Beds
  • 2.5 Baths
  • 2,045 Sq Ft

  11 Casarena Ct, Winter Haven, FL 33881

  Discover a rare opportunity to own this architecturally distinctive 2-bedroom, 2.5-bath residence located in the gated community of Casarean on the Lakes. This well-designed home offers an impressive blend of indoor and outdoor living spaces. The main level features a formal living room with a fireplace and wet bar, a dining area, a functional kitchen with breakfast bar, a guest half bath, and

  Tim Weisheyer DREAM BUILDERS REALTY

  11 Casarena Ct, Winter Haven, FL 33881
• 

  

  /17

  $1,600 per month

  • 3 Beds
  • 2 Baths
  • 1,035 Sq Ft
  • Apartment for Rent

  328 Avenue D SE, Winter Haven, FL 33880

  LOCATION, LOCATION, LOCATION...This 3 bedroom 2 bathroom end unit offers a private fenced backyard. Renovated last year with new roof, HVAC system, energy efficient tankless hot water heater, paint, baseboards and more. Featuring luxury vinyl floors throughout, upgraded cabinets and granite countertops in the kitchen. The bathrooms both feature walk in showers, vanities and fixtures. This unit is

  Kathryn Shevlin THE PROPERTY FIRM

  328 Avenue D SE, Winter Haven, FL 33880
• 

  /2

  $260,000 Sold Jun 02, 2025

  • 1,332 Sq Ft
  • $195/SF
  • 205 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2024

  724 Avenue R NE, Winter Haven, FL 33881

  BUYER FINANCING FELL THROUGH X 2! BACK ON THE MARKET AND UP TO $5000 DOLLARS IN CLOSING COST ASSISTANCE. BEAUTIFUL 3BR/2BA/1CG 1,332SF NEW CONSTRUCTION HOME CONVENIENTLY LOCATED IN WINTER HAVEN. CLOSE PROXIMITY TO TAMPA, ORLANDO, HWY 27, AND I-4. SOME EXTERIOR FEATURES OF THIS GORGEOUS PROPERTY INCLUDE: 30 YR ARCHITECTURAL SHINGLES, 8' EXTERIOR DOORS, STONE COLUMNS, HARDY SIDING, AND BEAUTIFUL

  Stephenie Long J&S PROPERTY REALTY GROUP LLC

  724 Avenue R NE, Winter Haven, FL 33881
• 

  

  /13

  Est $311,714 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,820 Sq Ft

  131 Krenson Bay Loop, Winter Haven, FL 33881

  131 Krenson Bay Loop, Winter Haven, FL 33881
• 

  

  /28

  $235,000

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft

  1904 3rd St NE, Winter Haven, FL 33881

  Welcome home to this beautifully updated 4 bed, 2 bath in the heart of Winter Haven! Inside you’ll find stylish upgrades like vinyl flooring, granite countertops, and stainless steel appliances. A brand new roof offers peace of mind, and the inviting side yard is perfect for gatherings, gardening, or simply relaxing in the Florida sun. With ~1,400 sq ft, this move-in ready home is ideal for

  Henry Linder XPERT REALTY GROUP

  1904 3rd St NE, Winter Haven, FL 33881
• 

  

  /10

  $800 per month

  • 2 Beds
  • 1 Bath
  • 683 Sq Ft
  • Apartment for Rent

  720 6th St NW Unit 4, Winter Haven, FL 33881

  Rent with confidence from a licensed Real Estate Brokerage. We have a quick and simple application process. WE PROUDLY WELCOME ALL PETS. Contact us through this Web site or call to set up a tour and apply today!Welcome to this cute 2 bed, 1 bath home! Our spacious layout is perfect for comfortable living. Enjoy the yard to unwind after a long day, enjoy the fresh air, and gather for

  Erich Spivey ALABAMA LLC

  720 6th St NW Unit 4, Winter Haven, FL 33881
• 

  /2

  $171,000 Sold May 30, 2025

  • 1,608 Sq Ft
  • $106/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1965

  620 Oleander Dr SE, Winter Haven, FL 33880

  **Buyers' Highest and Best is now due by Midnight on Saturday, April 26, 2025** Must See 3-Bedroom, 2-Bath Home in a Prime Winter Haven Location! Discover the potential of this 1,608 sq. ft. heated home, nestled on a 0.25-acre fenced lot. This property features 3 spacious bedrooms and 2 baths and offers a fantastic opportunity for those looking to add their personal touch. Located in an

  Felicia Gaffney XCELLENCE REALTY, INC

  620 Oleander Dr SE, Winter Haven, FL 33880
• 

  

  /16

  Est $311,194 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,820 Sq Ft

  143 Krenson Bay Loop, Winter Haven, FL 33881

  143 Krenson Bay Loop, Winter Haven, FL 33881
• 

  

  /14

  $28,900

  • 3 Beds
  • 2 Baths

  64Tower Manor Cir E Unit 64, Auburndale, FL 33823

  Auburndale Estates, a professionally managed, well-maintained manufactured home community, currently has a 1066 sq. ft. home with 3 bedrooms and 2 bathrooms for sale. Take advantage of this offer now and live in one of the state's most attractive areas. Call and schedule a viewing of this home and ask about our flexible financing options!

  Rob Mathis Auburndale Estates

  64Tower Manor Cir E Unit 64, Auburndale, FL 33823
• 

  

  /72

  $2,500 per month

  • 4 Beds
  • 3 Baths
  • 2,135 Sq Ft
  • House for Rent

  202 Lake Howard Dr NW, Winter Haven, FL 33880

  One or more photo(s) has been virtually staged. Escape to this stunning 4-bedroom, 2.5-bathroom lake house perfectly situated on the shores of Lake Howard! This spacious home boasts an open floorplan with a thoughtful split-bedroom layout, offering both comfort and privacy for your family or guests.Step inside and be greeted by tons of natural light streaming through expansive windows

  David Small KELLER WILLIAMS REALTY SMART 1

  202 Lake Howard Dr NW, Winter Haven, FL 33880
• 

  /2

  $480,000 Sold May 30, 2025

  • 2,093 Sq Ft
  • $229/SF
  • 2 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 2025

  227 Avenue A NE, Winter Haven, FL 33881

  Under Construction. This spacious townhome duplex offers an incredible opportunity for multi-generational living or investment potential. Each side features 5 bedrooms and 3 bathrooms, providing ample space for families of all sizes. On the first floor, you'll find an open-concept kitchen, dining area, and great room, creating a perfect space for entertaining. The kitchen boasts Samsung stainless

  Stephanie Morales THE REALTY EXPERIENCE POWERED BY LRR

  227 Avenue A NE, Winter Haven, FL 33881
• 

  

  /11

  Est $312,742 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,820 Sq Ft

  247 Krenson Bay Loop, Winter Haven, FL 33881

  247 Krenson Bay Loop, Winter Haven, FL 33881
• 

  

  /69

  $797,500

  • 4 Beds
  • 2.5 Baths
  • 2,710 Sq Ft

  1360 Mirror Terrace NW, Winter Haven, FL 33881

  AN AMAZING 4 BEDROOM 2.5 BATHROOM HOME SITUATED ON AN OVERSIZED (.71) AC LOT ON WINTER HAVEN'S FAMOUS CHAIN OF LAKES!!! This home on Spring Lake has amazing water views from the inside of nearly all rooms and especially from the 850 Sq Ft. covered screened patio with oversized pool. Enjoy the shade in both the front and back yards provided by the beautiful oaks while you appreciate the lake

  Bryan Dicks COLDWELL BANKER REALTY

  1360 Mirror Terrace NW, Winter Haven, FL 33881
• 

  /2

  $210,000 Sold May 30, 2025

  • 828 Sq Ft
  • $254/SF
  • 198 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1951

  960 Drexel Ave NE, Winter Haven, FL 33881

  R E D U C E D !!!! GREAT LOCATION , ONE BLOCK OFF WEST SIDE OF LAKE ELBERT , NO HOA. GREAT 2 BEDROOM - 1 BATH HOME WITH WOOD FLOORS.NEWER WINDOWS, ROOF, WATER HEATER, AND NEW AC. STEP INTO THIS 18X11 LIVING ROOM CONVENIENT TO EAT IN KITCHEN, EQUIPPED WITH RANGE, REFRIGERATOR, DISHWASHER AND MICROWAVE. THE BONUS ROOM OFF THE KITCHEN GIVES YOU EASY ACCES TO THE SCREEN ENCLOSED 16X14 FT

  Glenda Pruitt FLORIDA HOME CHOICE REALTY

  960 Drexel Ave NE, Winter Haven, FL 33881
• 

  

  /41

  Est $446,814 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,690 Sq Ft

  501 W Lake Elbert Dr NE, Winter Haven, FL 33881

  501 W Lake Elbert Dr NE, Winter Haven, FL 33881
• 

  

  /14

  $195,000

  • 3 Beds
  • 3 Baths
  • 1,786 Sq Ft

  505 Avenue G SE, Winter Haven, FL 33880

  Ideal Owner-Occupant Opportunity with Rental Income Potential! This unique property offers flexibility and income potential, making it perfect for an owner-occupant or savvy investor. The main home has been thoughtfully divided into two separate units, totaling over 1,785 square feet of living space. Easily reconfigured back into a single-family layout if desired. A detached rear garage has been

  Reggie Ward PREMIER REALTY OF TAMPA

  505 Avenue G SE, Winter Haven, FL 33880
• 

  /2

  $230,000 Sold May 28, 2025

  • 1,325 Sq Ft
  • $174/SF
  • 24 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1964

  1660 10th St SE, Winter Haven, FL 33880

  One or more photo(s) has been virtually staged. NEW ON THE MARKET - This charming 2-bedroom, 2-bathroom block home is just 7 minutes from Legoland and less than a mile from WalMart. Property offers great potential for Airbnb or long-term rental income. Priced competitively, it's the perfect opportunity for a first-time homebuyer or savvy investor. The home offers the possibility to easily convert

  Stephanie Meyer LPT REALTY, LLC

  1660 10th St SE, Winter Haven, FL 33880
• 

  

  /26

  Est $295,155 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  235 Krenson Bay Loop, Winter Haven, FL 33881

  235 Krenson Bay Loop, Winter Haven, FL 33881
• 

  

  /37

  $389,000

  • 4 Beds
  • 2 Baths
  • 2,292 Sq Ft

  710 Avenue T SE, Winter Haven, FL 33880

  Welcome to this modernly updated Mid-Century home, perfectly blending timeless charm with contemporary comforts. This spacious residence offers 4 bedrooms and 2 bathrooms across 2,292 square feet of thoughtfully designed living space. Step inside to an open great room plan featuring stunning Terrazzo flooring that flows seamlessly throughout the main areas, creating a bright and inviting

  Dee Norris NEXTHOME NORRIS & COMPANY REALTY

  710 Avenue T SE, Winter Haven, FL 33880
• 

  /2

  $255,000 Sold May 27, 2025

  • 1,519 Sq Ft
  • $168/SF
  • 84 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1966

  1360 10th Ct NE, Winter Haven, FL 33881

  Renovated 3/2 with enclosed pool and 2 car garage. One of the cheapest enclosed pool homes in the area. House is move-in ready.

  Ralph Harvey LISTWITHFREEDOM.COM

  1360 10th Ct NE, Winter Haven, FL 33881
• 

  

  /38

  Est $306,204 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,820 Sq Ft

  243 Krenson Bay Loop, Winter Haven, FL 33881

  243 Krenson Bay Loop, Winter Haven, FL 33881
• 

  

  /33

  $223,000

  • 2 Beds
  • 1 Bath
  • 1,240 Sq Ft

  411 Avenue A SE, Winter Haven, FL 33880

  A HONEY FOR THE MONEY! A well-built and beautifully maintained concrete block-single story home offering 2 bedrooms with an option for a third bedroom with bonus room conversion. A real cooks kitchen with all appliances, easy close cabinet doors, and an open and entertaining floor plan. Updated throughout; newer laminate flooring throughout, and new roof in 2023. Exterior offers a one-car

  Penny Miller NUWAVE REALTY

  411 Avenue A SE, Winter Haven, FL 33880
• 

  /2

  $70,000 Sold May 26, 2025

  • Land
  • 0.39 Acre
  • $179,487 per Acre

  • 33 Days On Market

  813 Lake Elbert Park NE, Winter Haven, FL 33881

  .39 acre lot - possible 2 buildable lots - walking distance to Lake Ebert Boat Ramp & Rotary Park. Partially cleared and a gorgeous lot. There is a dirt road access and minimal traffic. High & Dry & Not in a flood zone. A previous house was on the lot 30+ years ago

  Angie Inzerillo BLUE SUN REALTY LLC

  813 Lake Elbert Park NE, Winter Haven, FL 33881
• 

  

  /31

  Est $290,208 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  231 Krenson Bay Loop, Winter Haven, FL 33881

  231 Krenson Bay Loop, Winter Haven, FL 33881

Showing Results 161 - 200, Page 5 of 18